p-Xylylene dichloride
triethyl phosphite
tetraethyl 1,4-xylylenediphosphonate
Conditions | Yield |
---|---|
for 24h; Reflux; | 99% |
Heating; | 98.6% |
at 147 - 159℃; Arbuzov reaction; | 98% |
1,4-bis(bromomethyl)benzene
triethyl phosphite
tetraethyl 1,4-xylylenediphosphonate
Conditions | Yield |
---|---|
at 185℃; for 6h; Arbusov reaction; | 97% |
for 5h; Inert atmosphere; Reflux; | 96% |
for 10h; Michaelis-Arbuzov reaction; Heating; | 93% |
1,4-bis(bromomethyl)benzene
triethyl phosphate
tetraethyl 1,4-xylylenediphosphonate
Conditions | Yield |
---|---|
for 5h; Reflux; Inert atmosphere; Schlenk technique; | 96% |
ethyl bromide
1.4-dibromobenzene
triethyl phosphite
tetraethyl 1,4-xylylenediphosphonate
Conditions | Yield |
---|---|
at 130℃; for 2h; | 89% |
Conditions | Yield |
---|---|
With triethyl phosphite for 8h; Heating / reflux; | 86.4% |
With triethyl phosphite for 8h; Heating / reflux; | 86.4% |
1,4-bis(bromomethyl)benzene
triethyl phosphite
A
tetraethyl 1,4-xylylenediphosphonate
B
4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl
Conditions | Yield |
---|---|
at 120℃; for 3h; | A 11.8% B 48.5% |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 4.33 g / N-bromosuccinimide; azoisobutyronitrile / CCl4 / Heating 2: 5.24 g / 5 h / 160 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium bromate; sodium hydrogensulfite / water; ethyl acetate / 5 h 2: 16 h / 150 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium bromate; sodium hydrogensulfite / water; ethyl acetate / 5 h 2: 16 h / 150 °C View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 1,1'-azobis(1-cyanocyclohexanenitrile) / benzene / 8 h / Reflux 2: benzene / 6 h / 120 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / NBS; dibenzoyl peroxide / CCl4 / 4 h / Heating 2: 93 percent / 10 h / Heating View Scheme |
tetraethyl 1,4-xylylenediphosphonate
3-(trifluoromethoxy)benzaldehyde
Conditions | Yield |
---|---|
With sodium methylate In methanol; N,N-dimethyl-formamide at 80℃; for 2h; Horner-Wadsworth-Emmons reaction; | 99% |
tetraethyl 1,4-xylylenediphosphonate
4-methyl-benzaldehyde
(E,E)-4-methyl-4'-(4''-methylstyryl)stilbene
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 97% |
With potassium tert-butylate In tetrahydrofuran at 80℃; for 1h; | 68% |
Conditions | Yield |
---|---|
With hydrogenchloride In water for 20h; Reflux; | 96% |
With hydrogenchloride; water for 15h; Reflux; | 81.7% |
With hydrogenchloride; water for 12h; Hydrolysis; Heating; | 77% |
With hydrogenchloride at 150℃; | |
With hydrogenchloride Heating; | 0.65 g |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -70℃; for 12h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With sodium t-butanolate In tetrahydrofuran at -78 - 20℃; Horner-Wadsworth-Emmons Olefination; | 94% |
tetraethyl 1,4-xylylenediphosphonate
N,N-bis(4-bromophenyl)aminobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: tetraethyl 1,4-xylylenediphosphonate With sodium t-butanolate In ethanol; water; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: N,N-bis(4-bromophenyl)aminobenzaldehyde In N,N-dimethyl-formamide at 0℃; for 4.5h; | 92.3% |
Conditions | Yield |
---|---|
Stage #1: C38H35NO2; tetraethyl 1,4-xylylenediphosphonate; benzaldehyde With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Wittig-Horner reaction; Stage #2: With O,O-diethyl benzylphosphonate In tetrahydrofuran at 20℃; for 1h; Stage #3: With acetic acid In tetrahydrofuran | 92% |
Conditions | Yield |
---|---|
With sodium methylate In methanol; N,N-dimethyl-formamide Horner-Wadsworth-Emmons Olefination; Heating; | 92% |
tetraethyl 1,4-xylylenediphosphonate
4-methoxy-benzaldehyde
(E,E)-1,4-bis[2-(4-methoxyphenyl)-ethenyl]benzene
Conditions | Yield |
---|---|
With sodium methylate In methanol; N,N-dimethyl-formamide at 80℃; for 2h; Horner-Wadsworth-Emmons reaction; | 91% |
With sodium methylate |
4-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]-benzaldehyde
tetraethyl 1,4-xylylenediphosphonate
E,E-1,4-bis-4,4'-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)styrylbenzene
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 12.75h; | 91% |
tetraethyl 1,4-xylylenediphosphonate
3,4-dimethoxy-benzaldehyde
1,1'-{1,4-phenylenebis[(E)-ethen-2,1-diyl]}bis(3,4-dimethoxybenzene)
Conditions | Yield |
---|---|
Stage #1: tetraethyl 1,4-xylylenediphosphonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-dimethoxy-benzaldehyde In N,N-dimethyl-formamide at 10 - 65℃; for 26.5h; Wittig-Horner Reaction; Inert atmosphere; | 91% |
With sodium hydride In tetrahydrofuran at 20℃; for 13h; Horner-Wadsworth-Emmons Olefination; | 44% |
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 20 - 50℃; Horner-Wadsworth-Emmons reaction; | 90% |
3,5-dimethylbenzaldehyde
tetraethyl 1,4-xylylenediphosphonate
1,4-bis(3,5-dimethylstyryl)benzene
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 70℃; | 89.4% |
Conditions | Yield |
---|---|
With sodium t-butanolate In tetrahydrofuran at -78 - 20℃; Horner-Wadsworth-Emmons Olefination; | 89% |
2,5-bis(octyloxy)-4-(4-[2,2′:6′,2″]terpyridin-4′-ylphenylethynyl)benzaldehyde
tetraethyl 1,4-xylylenediphosphonate
Conditions | Yield |
---|---|
With potassium tert-butylate In toluene for 12h; Horner-Wadsworth-Emmons olefination; Reflux; | 88% |
tetraethyl 1,4-xylylenediphosphonate
3,4-ethylenedioxythiophene-2-carboxaldehyde
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 10h; Condensation; Wittig-Horner; | 87% |
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide for 0.5h; Horner-Wadsworth-Emmons reaction; Heating; | 87% |
With potassium tert-butylate In N,N-dimethyl-formamide at 20 - 50℃; Horner-Wadsworth-Emmons reaction; | 87% |
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 12h; Wittig-Horner reaction; Inert atmosphere; | 86% |
With sodium ethanolate In N,N-dimethyl-formamide at 60℃; for 2h; Wittig-Horner condensation; | 77% |
With sodium hydride In tetrahydrofuran at 66℃; for 2h; Wadsworth-Emmons condensation; | 66% |
tetraethyl 1,4-xylylenediphosphonate
4-((E)-2-[4-[(E)-2-(pyridin-4-yl)vinyl]phenyl]vinyl)pyridine
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Horner olefination; | 87% |
Stage #1: tetraethyl 1,4-xylylenediphosphonate With potassium tert-butylate In tetrahydrofuran at -10℃; for 0.333333h; Stage #2: pyridine-4-carbaldehyde In tetrahydrofuran at 20℃; for 16h; | 30% |
4,4′-bis(9-carbazolyl)benzophenone
tetraethyl 1,4-xylylenediphosphonate
C82H54N4
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; Wittig-Horner reaction; Inert atmosphere; | 87% |
tetraethyl 1,4-xylylenediphosphonate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; for 5h; Wittig-Horner Reaction; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 70 - 75℃; for 24h; Inert atmosphere; | 87% |
tetraethyl 1,4-xylylenediphosphonate
4-dimethylamino-benzaldehyde
N-4-[(E)-2-(4-(E)-2-[4-(dimethylamino)phenyl]vinylphenyl)vinyl]phenyl-N,N-dimethylamine
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 20 - 50℃; Horner-Wadsworth-Emmons reaction; | 86% |
With sodium methylate |
tetraethyl 1,4-xylylenediphosphonate
2,4-bis(trifluoromethyl)benzaldehyde
Conditions | Yield |
---|---|
With sodium methylate In methanol; N,N-dimethyl-formamide Horner-Wadsworth-Emmons Olefination; Heating; | 86% |
Conditions | Yield |
---|---|
With sodium methylate In methanol; N,N-dimethyl-formamide at 80℃; for 2h; Horner-Wadsworth-Emmons reaction; | 85% |
1,1,1-trifluoroacetophenone
tetraethyl 1,4-xylylenediphosphonate
C24H16F6
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; Inert atmosphere; | 85% |
This chemical is called Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester, and its CAS registry number is 4546-04-7. With the molecular formula of C16H28O6P2, its molecular weight is 378.34. It should be sealed in the cool and dry place, away from the light. Additionally, the product categories of this chemical are Electronic Chemicals; Horner-Emmons Reaction; Synthetic Organic Chemistry; Wittig & Horner-Emmons Reaction.
Other characteristics of the Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester can be summarised as followings: (1)ACD/LogP: 1.91; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.91; (4)ACD/LogD (pH 7.4): 1.91; (5)ACD/BCF (pH 5.5): 16.54; (6)ACD/BCF (pH 7.4): 16.54; (7)ACD/KOC (pH 5.5): 259.38; (8)ACD/KOC (pH 7.4): 259.38; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 90.68 Å2; (13)Index of Refraction: 1.484; (14)Molar Refractivity: 93.87 cm3; (15)Molar Volume: 327.8 cm3; (16)Polarizability: 37.21×10-24cm3; (17)Surface Tension: 39.5 dyne/cm; (18)Density: 1.153 g/cm3; (19)Flash Point: 263.7 °C; (20)Enthalpy of Vaporization: 72.84 kJ/mol; (21)Boiling Point: 490.7 °C at 760 mmHg; (22)Vapour Pressure: 2.7E-09 mmHg at 25°C.
Production method of this chemical: The could be obtained by the reactants of 1,4-bis-chloromethyl-benzene and phosphorous acid triethyl ester. This reaction needs the heating. The yield is 98.6 %.
Uses of this chemical: The p-xylylene-bis-phosphonic acid could be obtained by the reactant of Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester. This reaction should be taken at the temperature of 150 °C.
When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1.SMILES: O=P(OCC)(OCC)Cc1ccc(cc1)CP(=O)(OCC)OCC
2.InChI: InChI=1/C16H28O6P2/c1-5-19-23(17,20-6-2)13-15-9-11-16(12-10-15)14-24(18,21-7-3)22-8-4/h9-12H,5-8,13-14H2,1-4H3
3.InChIKey: XTKQUBKFKSHRPS-UHFFFAOYAI
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